$49+ Cheap flights from Chesapeake, VA to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Mar 11 — Mar 181
1 adult, Economy
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Cheapest flights from Chesapeake to MassachusettsExplore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
Explore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Sun 2/227:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/6![Breeze Airways logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Mon 3/97:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Mon 2/237:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$127
This Breeze Airways deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Sun 3/227:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Thu 3/127:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:06 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Fri 7/246:00 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Multiple Airlines
Sun 2/222:27 pm
BDL
- ORF
1 stop20h 15m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$154
This Mytrip deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:41 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Sun 5/177:15 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Fri 3/137:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:31 pm
ORF
- BOS
1 stop28h 13m
Spirit Airlines
Mon 3/165:49 pm
BOS
- ORF
1 stop25h 57m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$173
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORF
- ACK
1 stop5h 21m
Delta
Wed 8/54:51 pm
ACK
- ORF
1 stop5h 36m
Delta
Deal found 2/6![Delta logo]()
$186
This CheapOair deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:24 am
ORF
- BOS
Nonstop1h 38m
Multiple Airlines
Sat 5/167:00 am
BOS
- ORF
1 stop9h 53m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$192
Best flights from Chesapeake to MassachusettsDiscover carefully curated flight deals from Chesapeake to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
Discover carefully curated flight deals from Chesapeake to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Sun 2/227:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/6![Breeze Airways logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:04 pm
ORF
- BDL
Nonstop1h 27m
Multiple Airlines
Mon 2/237:13 pm
BDL
- ORF
2 stops16h 52m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$163
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:15 pm
ORF
- BDL
1 stop3h 05m
Southwest
Wed 3/1112:20 pm
BDL
- ORF
2 stops10h 15m
Southwest
Deal found 2/8![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORF
- ACK
1 stop5h 21m
Delta
Wed 8/54:51 pm
ACK
- ORF
1 stop5h 36m
Delta
Deal found 2/6![Delta logo]()
$186
This CheapOair deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:45 am
ORF
- BOS
1 stop15h 16m
Spirit Airlines
Wed 3/115:27 am
BOS
- ORF
1 stop12h 59m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:55 pm
ORF
- BOS
1 stop4h 04m
United Airlines
Thu 4/96:00 am
BOS
- ORF
1 stop5h 54m
United Airlines
Deal found 2/8![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:31 pm
ORF
- BOS
1 stop5h 17m
American Airlines
Thu 2/265:49 am
BOS
- ORF
1 stop3h 48m
American Airlines
Deal found 2/6![American Airlines logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:24 am
ORF
- BOS
Nonstop1h 38m
JetBlue
Mon 5/48:50 am
BOS
- ORF
Nonstop1h 42m
JetBlue
Deal found 2/6![JetBlue logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Mon 2/237:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$127
This Breeze Airways deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Sun 3/227:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
- BDL
2 stops21h 34m
Multiple Airlines
Wed 3/410:19 am
BDL
- ORF
1 stop11h 31m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Fri 3/137:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$158
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/141:45 pm
ORF
- BOS
Nonstop1h 49m
Delta
Sun 3/158:50 am
BOS
- ORF
Nonstop1h 47m
Delta
Deal found 2/6![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:31 pm
ORF
- BOS
2 stops16h 17m
Spirit Airlines
Mon 3/165:49 pm
BOS
- ORF
1 stop25h 57m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:47 am
ORF
- BOS
1 stop5h 51m
United Airlines
Sun 6/75:45 am
BOS
- ORF
1 stop3h 43m
United Airlines
Deal found 2/6![United Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2611:48 am
ORF
- BOS
1 stop5h 31m
United Airlines
Sun 3/295:45 am
BOS
- ORF
1 stop3h 46m
United Airlines
Deal found 2/6![United Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:41 pm
ORF
- BOS
1 stop15h 42m
Spirit Airlines
Mon 3/169:45 am
BOS
- ORF
1 stop12h 02m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:00 am
ORF
- BOS
1 stop4h 15m
Delta
Sat 3/2811:15 am
BOS
- ORF
Nonstop1h 44m
Delta
Deal found 2/6![Delta logo]()
$227
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:36 am
ORF
- ACK
2 stops9h 52m
American Airlines
Wed 8/51:38 pm
ACK
- ORF
1 stop3h 52m
American Airlines
Deal found 2/6![American Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
ORF
- BOS
1 stop3h 51m
United Airlines
Fri 8/216:00 am
BOS
- ORF
1 stop3h 59m
United Airlines
Deal found 2/5![United Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:44 pm
ORF
- BOS
1 stop4h 13m
United Airlines
Wed 7/295:45 am
BOS
- ORF
1 stop3h 43m
United Airlines
Deal found 2/6![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:15 pm
ORF
- ALB
1 stop6h 44m
Delta
Wed 4/156:00 pm
ALB
- ORF
1 stop6h 37m
Delta
Deal found 2/6![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:50 am
ORF
- ALB
1 stop6h 22m
Delta
Wed 4/156:00 am
ALB
- ORF
1 stop6h 57m
Delta
Deal found 2/6![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:40 am
ORF
- ALB
1 stop6h 12m
Delta
Thu 3/125:50 am
ALB
- ORF
1 stop3h 35m
Delta
Deal found 2/6![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:10 am
ORF
- ALB
1 stop4h 00m
United Airlines
Mon 3/167:24 pm
ALB
- ORF
1 stop4h 22m
United Airlines
Deal found 2/7![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:27 pm
ORF
- ALB
1 stop7h 11m
Delta
Sat 6/136:30 pm
ALB
- ORF
1 stop5h 34m
Delta
Deal found 2/7![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:47 am
ORF
- ACK
1 stop4h 04m
United Airlines
Wed 8/53:49 pm
ACK
- ORF
1 stop5h 53m
United Airlines
Deal found 2/7![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:27 pm
ORF
- ALB
1 stop7h 11m
Delta
Sun 6/146:00 am
ALB
- ORF
1 stop6h 43m
Delta
Deal found 2/6![Delta logo]()
$327
Last-minute flights from Chesapeake to MassachusettsDiscover last-minute flight deals from Chesapeake to Massachusetts. Data last updated February 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Massachusetts. Data last updated February 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:04 pm
ORF
- BDL
Nonstop1h 27m
Multiple Airlines
Mon 2/237:13 pm
BDL
- ORF
2 stops16h 52m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$163
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Sun 2/227:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/6![Breeze Airways logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Mon 2/237:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:18 pm
ORF
- BDL
Nonstop1h 27m
Multiple Airlines
Sun 2/222:27 pm
BDL
- ORF
1 stop20h 15m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
- BDL
2 stops15h 06m
Multiple Airlines
Wed 3/410:19 am
BDL
- ORF
1 stop11h 31m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Mon 3/97:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Thu 3/127:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Fri 3/137:00 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$158
This CheapOair deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:45 am
ORF
- BOS
1 stop15h 16m
Spirit Airlines
Wed 3/115:27 am
BOS
- ORF
1 stop12h 59m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:31 pm
ORF
- BOS
1 stop28h 13m
Spirit Airlines
Mon 3/165:49 pm
BOS
- ORF
1 stop25h 57m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$173
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/141:45 pm
ORF
- BOS
Nonstop1h 49m
Delta
Sun 3/158:50 am
BOS
- ORF
Nonstop1h 47m
Delta
Deal found 2/6![Delta logo]()
$197
This Breeze Airways deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/209:18 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Sun 3/227:15 am
BDL
- ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$138
One-way flights from Chesapeake to MassachusettsSearch for one-way flight options from Chesapeake to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
Search for one-way flight options from Chesapeake to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
This Booking.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Deal found 2/6![Breeze Airways logo]()
$49
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:04 pm
ORF
- BDL
Nonstop1h 27m
Breeze Airways
Deal found 2/6![Breeze Airways logo]()
$60
This Trip.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:46 am
ORF
- BOS
1 stop13h 27m
Frontier
Deal found 2/5![Frontier logo]()
$74
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:45 am
ORF
- BOS
1 stop14h 48m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$75
This Trip.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
- BOS
1 stop28h 13m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$76
This Priceline deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:47 pm
ORF
- BOS
1 stop7h 39m
Frontier
Deal found 2/5![Frontier logo]()
$80
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:15 pm
ORF
- BDL
1 stop6h 10m
American Airlines
Deal found 2/6![American Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:31 pm
ORF
- BOS
1 stop21h 44m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/211:39 am
ORF
- BOS
2 stops29h 06m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$84
This Trip.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:31 pm
ORF
- BOS
1 stop28h 13m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:05 am
ORF
- BOS
1 stop28h 16m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$89
This Super.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:45 am
ORF
- BOS
1 stop10h 09m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$91
Find flight deals from Chesapeake to Massachusetts
Keep the following information in mind while searching for Chesapeake to Massachusetts flight deals. Data was last updated February 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $119 (Mytrip) |
One-way from | $49 (Booking.com) |
Popular in | November |
Cheapest in | July |
Average price | $316 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 9, 2026.
Use the filters below to find and compare flights from Chesapeake to Massachusetts that are best for you.
Fly from
Chesapeake
Fly to
Massachusetts
Route
Depart
Return
Price
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Fri 2/20
9:18 pm-10:45 pm
Nonstop1h 27m
Hartford Bradley Intl
Sun 2/22
7:15 am-8:53 am
Nonstop1h 38m
$119
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Fri 2/20
9:18 pm-10:45 pm
Nonstop1h 27m
Hartford Bradley Intl
Mon 2/23
7:00 am-8:38 am
Nonstop1h 38m
$127
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Fri 3/20
9:18 pm-10:45 pm
Nonstop1h 27m
Hartford Bradley Intl
Sun 3/22
7:15 am-8:53 am
Nonstop1h 38m
$138
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Thu 3/5
9:04 pm-10:31 pm
Nonstop1h 27m
Hartford Bradley Intl
Fri 3/13
7:00 am-8:38 am
Nonstop1h 38m
$158
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Thu 2/19
9:04 pm-10:31 pm
Nonstop1h 27m
Hartford Bradley Intl
Mon 2/23
7:13 pm-12:05 pm
2 stops16h 52m
$163
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Wed 2/25
7:31 pm-5:05 pm
2 stops21h 34m
Hartford Bradley Intl
Wed 3/4
10:19 am-9:50 pm
1 stop11h 31m
$165
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Thu 3/5
12:15 pm-3:20 pm
1 stop3h 05m
Hartford Bradley Intl
Wed 3/11
12:20 pm-10:35 pm
2 stops10h 15m
$179
NorfolkNantucket
ORF - ACK
ORFACK
Norfolk
Tue 8/4
6:00 am-11:21 am
1 stop5h 21m
Nantucket Memorial
Wed 8/5
4:51 pm-10:27 pm
1 stop5h 36m
$186
NorfolkBoston
ORF - BOS
ORFBOS
Norfolk
Thu 3/5
6:45 am-10:01 pm
1 stop15h 16m
Boston Logan Intl
Wed 3/11
5:27 am-6:26 pm
1 stop12h 59m
$196
NorfolkBoston
ORF - BOS
ORFBOS
Norfolk
Sat 3/14
1:45 pm-3:34 pm
Nonstop1h 49m
Boston Logan Intl
Sun 3/15
8:50 am-10:37 am
Nonstop1h 47m
$197
Showing 1-10 of 55 results
Best time to book a flight from Chesapeake to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chesapeake with our price prediction graph.
ORF-BDL
ORF-ACK
ORF-BOS
ORF-ALB
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chesapeake to Massachusetts
C6E-USMA
ORF-BDL
ORF-ACK
ORF-BOS
ORF-ALB
What is the cheapest month to book a flight from Chesapeake to Massachusetts?
Currently, July is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $50). Flying from Chesapeake to Massachusetts in November is currently the most expensive (average of $115). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from C6E to MA?
Find hourly flight availability from Chesapeake to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 9, 2026.
It’s optimal to fly from Chesapeake to Massachusetts in the morning. By choosing this option you can save up to 70% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Chesapeake to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Massachusetts. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chesapeake to Massachusetts flight should consider departing on Friday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated February 9, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and American Airlines from Chesapeake to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chesapeake to Massachusetts
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Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Chesapeake to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chesapeake and Massachusetts flights
Browse other Chesapeake and Massachusetts flight options. Last updated on February 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Chesapeake after your stay in Massachusetts
Chesapeake to Massachusetts flights
Consider these flights traveling from Chesapeake to Massachusetts.
Top 8 airlines flying from Chesapeake to Massachusetts
Discover the top 8 airlines that operate flights from Chesapeake to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$45 | Average$84 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$81 | Average$157 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$82 | Average$149 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$83 | Average$245 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$244 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$154 | Average$339 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$156 | Average$312 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$298 | FlexibilityNo cancel fee | On-time63% |